Reaktion #306793

Reaktionsgleichung

(S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate

(R)-t-Butylsulfinamide

→

tert-butyl (S)-1-(4-bromophenyl)ethyl((E)-4-((R)-tert-butylsulfinylimino)-4-phenylbutyl)carbamate

Ausbeute 51.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat reflux for overnight
3. 3
   Sonstigewas consumed
4. 4
   workup.ADDITIONThe mixture was diluted with ether (200 mL)
5. 5
   Waschenwashed with water (50 mL), brine (30 mL)
6. 6
   Trocknendried over Na2SO4
7. 7
   FiltrationAfter filtration and concentration
8. 8
   Sonstigethe residue was purified by chromatography on a 120-g silica gel cartridge
9. 9
   Wascheneluted with a 10˜35% EtOAc in hexanes gradient

Vorschrift

(S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate (3.14 g, 7.04 mmol), (R)-t-Butylsulfinamide, Ti(OEt)4 (125 μL, 1.5 equiv) were mixed with dry THF (80 mL) and heated at reflux for overnight. LC-MS found most of starting material was consumed. The mixture was diluted with ether (200 mL), washed with water (50 mL), brine (30 mL), dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 120-g silica gel cartridge, eluted with a 10˜35% EtOAc in hexanes gradient, to afford tert-butyl (S)-1-(4-bromophenyl)ethyl((E)-4-((R)-tert-butylsulfinylimino)-4-phenylbutyl)carbamate (1.97 g, 51%) product and recovered starting material (0.72 g). LC-MS Method 1 tR=2.43 min, m/z 549, 551 (M+1)

Quelle